2-(Hydroxymethyl)-5-methylbenzoic acid → 2-Formyl-5-methylbenzoic acid

HRID 2361333Notes

Reaction equation

HRID 2361333 reaction equation
[OH:1][CH2:2][C:3]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]>C1COCC1.O=[Mn]=O>[CH:2]([C:3]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])=[O:1]

Participants

4

Reactant 1

HCID 679628172-(Hydroxymethyl)-5-methylbenzoic acid

Product 1

HCID 772303602-Formyl-5-methylbenzoic acidYield 52.8%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

To a homogeneous, colorless solution of 2-(hydroxymethyl)-5-methylbenzoic acid (0.6325 g, 3.81 mmol) in THF (35 mL) under nitrogen was added MnO2 (4.96 g, 57.1 mmol), and the reaction was stirred overnight. Additional MnO2 (˜3 g) was added, and the reaction was stirred overnight. The mixture was filtered through a pad of CELITE® and rinsed with THF. The filtrate was concentrated in vacuo to give the desired product (0.3302 g, 2.011 mmol, 52.8% yield) as an off-white solid.

Workup

  1. stirringthe reaction was stirred overnight
  2. filtrationThe mixture was filtered through a pad of CELITE®
  3. washrinsed with THF
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-98609ee8b0e24affb9a2c228cb1387aa
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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